Meeting at the Crossroads podcast

About Meeting at the Crossroads podcast

Every business owner reaches a crossroads. Should I grow or hold steady? Is it time to step back or am I not ready? Do I stay, sell, merge, reinvent or start again? It's not if you reach a crossroads. It's when. Meeting at the Crossroads is the podcast where business owners and directors share the real, unfiltered stories behind the decisions that defined them, moments of growth, exit, retirement, reinvention, and uncertainty, and how they found a way through. I'm Sarah Daly, a qualified accountant, transition facilitator, executive coach, and business consultant. I've started, grown, and sold my own business, and I've stood at a few crossroads of my own. This podcast is my way of making sure no business owner has to face those moments without the benefit of hearing someone else's story first. Because we all have something to learn from each other. No matter your age, your stage, or the size of your business. Short episodes. Honest conversations. Real experience. Find me on Instagram at sarahdalycoaching, on LinkedIn as Sarah Daly, or at sarahdaly.com. Hosted on Acast. See acast.com/privacy (https://acast.com/privacy) for more information.

Publisher

Sarah Daly

Category

business · business · business

Language

en

Explicit

No

First episode

19 May 2026

Latest episode

29 Oct 2026

Latest episodes

7 episodes in the feed.

1. 

   29 Oct 2026

   Creating Your Own Crossroads With Ciarán Casey, Part Two

   This is the final episode in this two-part special, where Sarah sits down with Ciarán Casey, Director of My Learning Limited and author of Leadership in Tune. Ciaran picks up with what might be his most unexpected pivot yet: leaving the safety of financial services to take over his sister's media business, an industry and product set he knew nothing about, in the middle of digital disruption. He talks candidly about navigating a business in "free fall," the value of asking "stupid questions," and eventually selling the business into a US company. In this episode, you’ll discover: Taking over his sister's magazine business with zero industry or product knowledge The advantage of being an outsider: asking the "stupid questions" that mattered most Why Ciaran resists identifying as "an entrepreneur" or "a financial services expert", and what he says defines him instead The gap between leaders' good intentions and how they're actually experienced, and what Gallup's engagement data reveals Why leadership doesn't reside within a person but emerges between people Introducing the Conscious Relational Impact Model from Leadership in Tune Meeting at the Crossroads is available on Apple Podcasts, Spotify, and wherever you get your podcasts. If today's episode resonated with you, share it with a fellow business owner who might be standing at their own crossroads. Connect with Sarah LinkedIn (https://www.linkedin.com/in/sarahdaly1/) Website (https://www.sarahdaly.com/) Instagram (https://www.instagram.com/sarahdalycoaching) Connect with Ciarán LinkedIn (https://www.linkedin.com/in/ciaran-casey-3319099/) Website (https://leadershipintune.net/) Hosted on Acast. See acast.com/privacy (https://acast.com/privacy) for more information.

2. 

   21 Oct 2026

   Creating Your Own Crossroads With Ciarán Casey, Part One

   This is the first episode in this two-part special, where Sarah sits down with Ciarán Casey, Director of My Learning Limited and author of Leadership in Tune. In part one, Ciaran walks us through his career, from programming on IBM systems in the 1980s, through GE Capital, a startup venture with his brother, and back into corporate life at First Active. Ciaran has moved across five or six industries over a three-decade career, a pattern most people avoid, choosing instead to build deep expertise in one lane. In this conversation, he unpacks what actually drove those moves: not ambition or a grand plan, but a restlessness with stability and a constant pull toward growth and challenge. Along the way, Ciaran shares the personal framework he uses for big decisions: weighing not which choice avoids regret, but which regret is easier to live with. In this episode, you’ll discover: Why Ciaran believes stability doesn't equal fulfillment, and how boredom, not crisis, has driven most of his career moves The "exam question" he asks himself before any move: is there an opportunity for growth here? His end-of-year ritual of asking, "What did I learn this year?" Why the real danger isn't standing at a crossroads, it's staying too long on a comfortable road His most defining career pivot Introducing regret as a decision-making tool In part 2, Sarah and Ciarán dig deeper into his decision-making framework around regret, and the leadership model behind his book Leadership in Tune. Meeting at the Crossroads is available on Apple Podcasts, Spotify, and wherever you get your podcasts. If today's episode resonated with you, share it with a fellow business owner who might be standing at their own crossroads. Connect with Sarah LinkedIn (https://www.linkedin.com/in/sarahdaly1/) Website (https://www.sarahdaly.com/) Instagram (https://www.instagram.com/sarahdalycoaching) Connect with Ciarán LinkedIn (https://www.linkedin.com/in/ciaran-casey-3319099/) Website (https://leadershipintune.net/) Hosted on Acast. See acast.com/privacy (https://acast.com/privacy) for more information.

3. 

   23 Sept 2026

   Eliminating Blind Spots in Business with Frank Fleming

   Frank Fleming, CEO of Verifact, joins Sarah Daly to unpack the crossroads that reshaped his business: the 2015 decision to pivot from a consultancy into a full software company. Frank traces the mix of ambition and fear behind that leap, how his years as a commercial fisherman built his tolerance for risk and change, and the blind spots he only recognised in hindsight. He shares what he'd tell anyone facing a similar pivot today: build an MVP, get feedback early, and surround yourself with people who can show you what you can't see for yourself. In this episode, you’ll discover: Why a service business can hit a scalability ceiling and how to know when it's time to build something more scalable How to weigh the excitement of a big pivot against the fear of leaving a known, working business behind Why your past career can shape how you handle risk and change The concept of "blind spots" in decision-making, and practical ways to reduce them Why thinking about your total addressable market matters from day one, not after you've already built something How looking back on big decisions with hindsight can clarify what to do differently next time, without dwelling in regret Why building a trusted network of people to bounce ideas off is one of the most valuable things you can do as a founder Meeting at the Crossroads is available on Apple Podcasts, Spotify, and wherever you get your podcasts. If today's episode resonated with you, share it with a fellow business owner who might be standing at their own crossroads. Connect with Sarah LinkedIn (https://www.linkedin.com/in/sarahdaly1/) Website (https://www.sarahdaly.com/) Instagram (https://www.instagram.com/sarahdalycoaching) Connect with Frank LinkedIn (http://linkedin.com/in/frank-fleming-87217625) Website (https://vfact.com/) Hosted by Sarah Daly Edited by Amanda Fitzgerald Hosted on Acast. See acast.com/privacy (https://acast.com/privacy) for more information.

4. 

   26 Aug 2026

   Making Big Decisions Under Pressure with Dawn Coupe

   Dawn Coupe built Equinox Consulting from a single 3-month contract into a multi-million-pound consultancy over 11 years, growing the business tenfold in just 4 years. But behind the growth was a business barely holding together: contracts overrunning by hundreds of thousands of pounds, mounting supplier debt, and a company that had scaled faster than its systems could support. Dawn shares what it really took to walk away from a deal that looked like a lifeline, how she rebuilt trust with her leadership team, and the lesson she now carries into her coaching work with founders who've built something brilliant and lost themselves inside it. In this episode, you’ll discover: Why rapid growth can be as dangerous as decline How to spot a "helpful" offer that isn't A simple way to test any high-stakes decision Why your busiest, most stressed moment is the worst time to sign anything The real cost of carrying a crisis alone How to build a support network before you need one What recovery actually looks like The mindset shift that changes everything Meeting at the Crossroads is available on Apple Podcasts, Spotify, and wherever you get your podcasts. If today's episode resonated with you, share it with a fellow business owner who might be standing at their own crossroads. Connect with Sarah LinkedIn (https://www.linkedin.com/in/sarahdaly1/) Website (https://www.sarahdaly.com/) Instagram (https://www.instagram.com/sarahdalycoaching) Connect with Dawn LinkedIn (https://www.linkedin.com/in/dawn-coupe/) Website (https://www.equinoxcl.com/) Hosted on Acast. See acast.com/privacy (https://acast.com/privacy) for more information.

5. 

   22 Jul 2026

   Rebuilding after Burnout with Leadership Strategist Charley Swords

   For 29 years, leadership strategist Charley Swords has asked leaders one essential question: not what are you trying to achieve, but how are you actually leading? But this episode isn't about the leaders she's coached, it's about her own crossroads. After years of relentless international travel, a health scare forced Charley to stop completely. A visit to her GP delivered words she'll never forget: get on a plane, and you'll come off it in a box. What followed was an 18-month recovery, the closure of her limited company, and a hard look at whether to retire, return to employment, or start again. Charley talks candidly about resilience, the myth that stepping back is a sign of weakness, and why she believes self, family, and work must stay in balance for anyone in business. In this episode, you’ll discover: How to recognise the warning signs your body sends before burnout forces a decision for you Why stepping back from a business is a sign of strength, not failure How to evaluate your real options when facing a health, career, or business crossroads A simple framework for keeping yourself, your family, and your work in balance Why closing or restructuring a business isn't the same as giving up How to rebuild momentum and confidence after an extended setback What to consider when facing more than one major life disruption in close succession Practical ways to adapt how you work when your usual way of operating is no longer possible Meeting at the Crossroads is available on Apple Podcasts, Spotify, and wherever you get your podcasts. If today's episode resonated with you, share it with a fellow business owner who might be standing at their own crossroads. Connect with Sarah LinkedIn (https://www.linkedin.com/in/sarahdaly1/) Website (https://www.sarahdaly.com/) Instagram (https://www.instagram.com/sarahdalycoaching) Connect with Charley LinkedIn (https://www.linkedin.com/in/charleyswords/) Website (https://leadershipcentreofexcellence.ie/) Hosted on Acast. See acast.com/privacy (https://acast.com/privacy) for more information.

6. 

   24 Jun 2026

   Trusting Your Gut in Business with Christina Clarkin

   What does it take to let go of a brand you built from scratch and merge it into something new? In this debut episode of Meeting at the Crossroads, Sarah sits down with marketing expert Christina Clarkin to explore one of the boldest decisions of her career, merging her solo business, The Marketing Lounge, with fellow industry experts Aidan and Jim to form MX3. In This Episode, You'll Discover Why Christina reached a growth ceiling in her solo business and what made her reluctant to simply hire How she and her future partners were "matchmade" by a mutual vendor, and what made the chemistry click What it really felt like to consider letting go of a brand she had built entirely on her own Why growth alone isn't always enough, and how to recognise when you've hit a ceiling you can't break through solo Why fear of letting go of your brand, your control, your identity as a business owner is normal, and how to work through it How to use your "why" as an anchor when doubt and outside opinion start to cloud your thinking Christina had built a profitable, well-respected business over four and a half years. But she'd hit a ceiling. When the opportunity to merge came knocking in late 2019, her gut said yes, and then COVID arrived. What followed was months of uncertainty, a house move, and a deeply personal decision about what kind of business owner she wanted to be. This is that story. If today's episode resonated with you, share it with a fellow business owner who might be standing at their own crossroads. Meeting at the Crossroads is available on Apple Podcasts, Spotify, and wherever you get your podcasts. Production by Amanda Fitzgerald. Connect with Sarah LinkedIn (https://www.linkedin.com/in/sarahdaly1/) Website (https://www.sarahdaly.com/) Instagram (https://www.instagram.com/sarahdalycoaching) Connect with Christina LinkedIn (https://www.linkedin.com/in/christinaclarkin/) Website (https://www.mx-3.ie/) Hosted on Acast. See acast.com/privacy (https://acast.com/privacy) for more information.

7. 

   19 May 2026

   Meeting at The Crossroads Trailer

   Every business owner faces moments that stop them in their tracks. Meeting at the Crossroads is the podcast that meets you in those moments. Hosted by Sarah Daly, a qualified accountant, transition facilitator, executive coach, and business consultant, each episode features candid, unfiltered conversations with business owners and directors who share the real stories behind their defining decisions. Short, honest, and grounded in lived experience , this podcast offers the kind of insight that's often only understood in hindsight. Whether you're on a commute, a coffee break, or facing a crossroads right now, we're here to make sure you never have to face those moments alone. Hosted on Acast. See acast.com/privacy (https://acast.com/privacy) for more information.

Contact Meeting at the Crossroads podcast

Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.